WO2000002886A1 - Derives silole et element organique electroluminescent les contenant - Google Patents

Derives silole et element organique electroluminescent les contenant Download PDF

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Publication number
WO2000002886A1
WO2000002886A1 PCT/JP1999/003671 JP9903671W WO0002886A1 WO 2000002886 A1 WO2000002886 A1 WO 2000002886A1 JP 9903671 W JP9903671 W JP 9903671W WO 0002886 A1 WO0002886 A1 WO 0002886A1
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group
bonded
organic
membered ring
layer
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Japanese (ja)
Inventor
Manabu Uchida
Toshihiro Koike
Takenori Izumizawa
Kenji Furukawa
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JNC Corp
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Chisso Corp
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Priority to DE69929067T priority Critical patent/DE69929067D1/de
Priority to EP99929736A priority patent/EP1113017B1/fr
Priority to US09/743,426 priority patent/US6376694B1/en
Publication of WO2000002886A1 publication Critical patent/WO2000002886A1/fr
Anticipated expiration legal-status Critical
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene

Definitions

  • the present invention relates to a silole derivative that can be expected to be widely applied to electronic functional materials, optical functional materials, and the like, and an organic electroluminescent device using the same.
  • One of the typical ⁇ -electron organic compounds among these is a group of ⁇ -electron organic compounds having a 5-membered ring structure in the basic structure, such as thiophene and pyrrole. ing.
  • a ⁇ -electron electron-accepting compound has been demanded.
  • JP-A-6-106669 and JP-A-6-166746 report that they are intended to be applied to conductive polymers.
  • Japanese Patent Application Laid-Open No. 9-87616 Japanese Patent Application Laid-Open No. 9-194487, Japanese Chemical Society 70th Annual Meeting Proceedings II, page 700, 2D10 2, the chemical Society of Japan, No. 7 0 spring annual meeting Preprint II, 7 0 1 page, 2 D 1 0 3, the chemical Society of Japan, No. 7 1 autumn annual meeting Preprint, 3 2 pages, 2 ⁇ 1 ct 2 1 Proceedings of the 71st Autumn Meeting of the Chemical Society of Japan, page 32, 2 P1 ⁇ 22, etc., report examples of application to organic EL devices utilizing the electron-accepting properties of silonole derivatives. Have been. these Among them, some compounds have moderate electron-accepting and electron-donating properties, and also have luminescent properties, so that they have been applied to luminescent materials. However, none of the compounds described in these publications has emission luminance sufficient for practical use.
  • the organic EL device has a structure in which an organic compound is sandwiched between two electrodes.
  • the organic compound used includes a charge transport material and a light emitting material.
  • luminescent materials with high luminous efficiency.
  • JP-A-7-179477 and JP-A-7-304489 disclose reactive silyl groups at the 2- and 5-positions of the silole ring, and provide various siloles. Although an example of synthesizing a derivative is shown, no description is given of luminescence.
  • German patent (DE 444 0 250) describes an example in which a spirosilol derivative is applied to an organic EL device, but there is no description about the luminescent properties of those compounds. Further, its structure is also limited to dibenzo derivatives, and there is no description regarding the synthesis method and physical properties of a compound having an asymmetric ring skeleton.
  • dichenosylol derivative had very poor performance and low practicality as a luminescent material for organic EL devices described in Chemistry Letters (1998, 1233).
  • the present invention has been made in view of the above-mentioned problems of the related art, and has as its object to provide a novel silole derivative having high luminous efficiency; and an organic EL using the silole derivative. It is to provide an element. Disclosure of the invention
  • the present inventors have solved the above-mentioned problems of the conventional organic EL device, and have conducted intensive studies on novel silole derivatives that lead to various functional materials, and as a result, have found a specific silonole derivative, and High luminous efficacy when the silole derivative is used It has been found that an organic EL device having a high efficiency can be obtained, and the present invention has been completed.
  • the present invention has the following configurations 1>, ⁇ 2>, 3>, ⁇ 4>, and especially 5>.
  • R 2 each independently represent a substituted or unsubstituted alkyl group, silyl group, aryl group, heterocyclic group, or alkenyl group, and may be bonded to each other at each end.
  • a rl and Ar 2 each independently represent a substituted or unsubstituted aryl or heterocyclic group; ⁇ ⁇ ! ⁇ .
  • Ru Rgo is each independently a substituted or unsubstituted alkyl Represents an aryl group, an aryl group or a heterocyclic group, and may be bonded to each other at each end.
  • ⁇ ⁇ ! ⁇ Each independently represents a substituted or unsubstituted alkyl group, aryl group or heterocyclic group, which may be bonded to each other at each end.
  • silole derivative represented by the general formula (1) of the present invention include compounds represented by the following chemical formulas (5) to (15).
  • the silole derivative of the present invention can be obtained, for example, by the following production method c, ie, a compound represented by the general formula (16)
  • F 2 and G 2 each independently represent a substituted or unsubstituted alkyl group, silyl group, aryl group, heterocyclic group, or alkenyl group, and are bonded to each other at each terminal
  • d each independently represents a substituted or unsubstituted aryl group or a heterocyclic group
  • 1 and 2 may be bonded to each other to form a 5- or 6-membered ring
  • G 2 may be bonded to each other to form a 5- or 6-membered ring
  • Y and Z each independently represent a halogen atom.
  • the silole derivative of the present invention By reacting a base with the gen derivative represented by the formula and then reacting with a silane derivative, the silole derivative of the present invention can be obtained.
  • examples of the base used include organic lithium reagents such as n-butyllithium, tert-butyllithium, and phenyllithium, and Grignard reagents such as magnesium and magnesium bromide.
  • the solvent used is not particularly limited as long as it is inert to these bases, and is usually a solvent such as getyl ether or tetrahydrofuran (hereinafter referred to as THF).
  • Useful ether solvents or aromatic solvents such as benzene and toluene are used.
  • the silole derivative of the present invention By reacting lithium metal with the acetylene derivative represented by the following formula and then reacting with a silane derivative, the silole derivative of the present invention, particularly the silole derivative represented by the general formula (2), can be obtained.
  • the solvent used is not particularly limited as long as it is inert to these bases, and usually includes an ether solvent such as getyl ether or THF.
  • the silane derivative used may be 9, 9- Examples include halogenated silafluorenes such as dichlorosilafnorolene, 2,7-di-tert-butynolene-1,9,9-dichlorosilafluorene, and alkoxysilanes such as 9,9-dimethoxysilafluorene.
  • halogenated silafluorenes such as dichlorosilafnorolene, 2,7-di-tert-butynolene-1,9,9-dichlorosilafluorene
  • alkoxysilanes such as 9,9-dimethoxysilafluorene.
  • the reaction is preferably carried out in an inert gas, and nitrogen and argon gases are used.
  • the reaction temperature is not particularly limited, but is usually preferably about ⁇ 78 ° C. to about 120 ° C.
  • the reaction time for this reaction may be stopped when the reaction has sufficiently proceeded.
  • the reaction may be tracked by a general analytical method such as NMR or chromatography, and the end point of the reaction may be determined at an optimum time.
  • silole derivative represented by the general formula (1) and the general formula (2) of the present invention can be synthesized by converting the obtained compound by a generally known synthesis method.
  • the substituent may be introduced before the formation of the silole ring, Guided after formation
  • Substituents attached to the thus obtained silole derivative of the present invention include alkyl groups such as methyl group, ethyl group, normal propyl group, isopropyl group, cyclopentyl group and tert-butyl group, butyl group and aryl group.
  • alkenyl groups such as butyryl and styryl groups, silinole groups such as trimethylsilyl group, dimethyl-tert-butynolesilyl group, trimethoxysilyl group and triphenylsilyl group, phenyl group, naphthyl group, anthracenyl group, biphenyl Group, tolyl group, pyrenyl group, perylenyl group, anysinole group, aryl group such as terphenyl group and phenanthrenyl group, hydrofuryl group, hydropyrenyl group, dioxanyl group, chenyl group, furyl group, oxazolyl group, oxaziazolyl group, thiazolyzolyl group Le And heterocycles such as thiadiazolyl group, acridinyl group, quinolyl group, quinoxaloyl group, phenanthrolinole group, benzochenyl group, benzocheny
  • substituents may be bonded to each other at any position to form a ring.
  • the silole derivative of the present invention can be expected to be widely applied not only to light-emitting materials but also to electronic functional materials and optical functional materials by utilizing electronic properties derived from silole rings.
  • the structure of the organic EL device of the present invention has various modes, it is basically represented by the general formula (1) and the general formula (2) between a pair of electrodes (anode and cathode). It has a structure in which an organic layer containing a silole derivative is sandwiched. If necessary, a hole injection material, a hole transport material, a light-emitting material, an electron injection material or an electron transport material, or the like is provided in the silole derivative layer. Can be added. Further, by adding another light-emitting material to this light-emitting layer, light of a different wavelength can be generated, and the light-emitting efficiency can be improved.
  • hole injection materials hole transport materials, luminescent materials, electron injection materials, electron transport materials, and the like may be used as hole injection layers, hole transport layers, luminescent layers, electron injection layers, and electron transport layers. It can also be laminated on the containing layer.
  • Specific configurations include (1) anode Z, the cathode of the silole derivative layer Z of the present invention, (2) anode / hole injection layer / cathode of the silole derivative layer of the present invention, and (3) anode Z, the silole of the present invention.
  • Derivative layer / electron injection layer / cathode (4) anode / hole injection layer Z Shironore derivative layer / electron injection layer Z cathode of the present invention, (5) anode Z hole injection layer / silole derivative layer of the present invention / Electron transport layer / interface layer / cathode, (6) anode / hole injection layer / hole transport layer / silole derivative layer of the present invention / electron injection layer Z cathode, (7) anode / hole injection layer / hole Examples of the layer structure include a transport layer / silole derivative layer of the present invention, a Z electron injection layer, a Z interface layer, and a cathode.
  • the hole injection layer, the electron injection layer, the hole transport layer, the electron transport layer, and the interface layer are not necessarily required, but by providing these layers, the luminous efficiency can be improved.
  • the organic EL device of the present invention is supported by a substrate in any of the above structures.
  • the substrate only needs to have mechanical strength, thermal stability and transparency, and glass, a transparent plastic film, or the like can be used.
  • metals, alloys, electrically conductive compounds, and mixtures thereof having a work function larger than 4 eV can be used.
  • Specific examples include metals such as Au, Cul, indium tin oxide (hereinafter referred to as ITO), conductive transparent materials such as Sn ⁇ 2 , and ZnO.
  • Cathode materials include metals, alloys, electrically conductive compounds, and mixtures thereof with work functions less than 4 eV. Specific examples include calcium, magnesium, lithium, aluminum, magnesium alloys, lithium alloys, and anolemminium alloys, and a mixture of aluminum z lithium, magnesium E.g. silver, magnesium / indium.
  • the electrodes In order to efficiently extract light emitted from the organic EL element, it is desirable that at least one of the electrodes has a light transmittance of 10% or more.
  • the sheet resistance as an electrode is preferably several hundred ⁇ mm or less.
  • the film thickness depends on the properties of the electrode material, it is usually 10 ⁇ ! 11 ⁇ m, preferably 10-400 nm.
  • Such an electrode can be manufactured by forming a thin film by a method such as evaporation or sputtering using the above-mentioned electrode substance.
  • the interface layer is preferably a layer that can promote the injection of electrons from the cathode, and a layer that prevents holes from flowing into the cathode, and is selected depending on the compatibility with the material used for the cathode. Specific examples include lithium fluoride, magnesium fluoride, calcium fluoride, and the like.
  • materials used such as a hole injection material, a hole transport material, a light emitting material, and an electron injection material preferably have a Tg of 80 ° C. or more, and more preferably a Tg of 100 ° C. More than C.
  • hole-injecting materials and hole-transporting materials used in the organic EL device of the present invention include those conventionally used as charge transporting materials for holes in photoconductive materials, and those for organic EL devices. Any known materials used in the hole injection layer and the hole transport layer can be selected and used.
  • sorbazole derivatives N-phenylcarbazole, polyvinylcarbazole, etc.
  • TPD triarylamine derivatives
  • 1,1-bis (4 -Di-p-tolylaminophenyl) cyclohexane 1,1-bis (4 -Di-p-tolylaminophenyl) cyclohexane, -Diphenyl- ⁇ -dinaphthyl-4,4'-diaminobiphenyl (hereinafter abbreviated as NPD), 4,4 ', 4''-tris ⁇ N- (3-methylphenyl) -N-phenylami No. Triphenylamine, Journal of the Chemical Society, Society, Chemical, Communication, p.
  • the hole injection layer and the hole transport layer in the organic EL device of the present invention may be composed of one or more layers containing one or more of the compounds described above. It may be a laminate of a plurality of contained layers. There are no particular restrictions on other electron injecting materials and electron transporting materials used in the organic EL device of the present invention. Among the photoconductive materials, those conventionally used as electron transfer compounds and those of the organic EL device can be used. Any of the known materials used for the layer and the electron transport layer can be selected and used.
  • Preferred examples of such electron transfer compounds include diphenylquinone derivatives (those described in the journal of the Institute of Electrophotography, 30, 3 (1991)) and perylene derivatives (J. Apply. Phys., 27, 269 (1988)). ), And oxadiazole derivatives (Jpn. J. Appl. Phys., 27, L713 (1988), Applied 'Physics. Letter, Appl. Phys. Lett.), 55, 1489 (1989). )), A thiophene derivative (as described in JP-A-4-1221286, etc.), a triazole derivative (as described in Jpn. J. Appl.
  • light-emitting materials used in the light-emitting layer of the organic EL device of the present invention include the daylight fluorescent light described in Polymer Functional Materials Series “Optical Functional Materials” edited by The Society of Polymer Science, Kyoritsu Shuppan (1991), p.236.
  • Known luminescent materials such as materials, fluorescent brighteners, laser dyes, organic scintillators, and various types of fluorescent analysis reagents can be used.
  • polycyclic condensed compounds such as anthracene, phenanthrene, pyrene, chrysene, perylene, coronene, rubrene, and quinacridone; oligophenylene compounds such as quarter phenyl; 1,4-bis (2-methylstyrinole) Benzene, 1,4-bis (4-methylstyryl) benzene, 1,4-bis (4-methyl-5-phenyl-2-oxazolyl) benzene, 1,4-bis (5-phenyl-2- Oxazolyl) benzene, 2,5-bis (5-tasalibutinole-2-benzoxazolyl) thiophene, 1,4-dipheninole-1,3-f, tajen, 1,6-diphenyl-1 , 3,5-hexatriene, 1,1,4,4-tetraphenyl-1,3-butadiene and other scintillators for liquid scintillation, metal
  • Each layer constituting the organic EL device of the present invention can be formed by forming a material constituting each layer into a thin film by a known method such as an evaporation method, a spin coating method, and a casting method.
  • the thickness of each layer formed in this way is not particularly limited and can be appropriately selected according to the properties of the material, but is usually selected in the range of 2 nm to 5000 nm.
  • the evaporation conditions vary depending on the type of silole derivative, the target crystal structure and association structure of the molecular accumulation film, etc., but in general, the port heating temperature is 50 to 400 ° C, and the degree of vacuum is ! 10- 6 ⁇ 10- 3 P a, deposition rate 0. 0: ⁇ 50 nm / sec, substrate temperature - 1 50 ten 300 ° C, film thickness 5 eta [pi! It is desirable to select an appropriate value within the range of 5 ⁇ m.
  • an organic EL device comprising the above-described anode / silole derivative layer / cathode A method for manufacturing an element will be described.
  • a thin film made of a material for an anode is formed by a vapor deposition method so as to have a thickness of ⁇ or less, preferably in a range of 10 to 200 nm to form an anode.
  • the production order can be reversed, and the cathode, the light-emitting layer, and the P-electrode can be produced in this order.
  • the anode When a DC voltage is applied to the organic EL device obtained in this manner, the anode may be applied with a positive polarity and the cathode may be applied with a single polarity, and when a voltage of about 2 to 40 V is applied, it is transparent or translucent. Light emission can be observed from the electrode side (anode or cathode, and both).
  • the organic EL element also emits light when an AC voltage is applied.
  • the waveform of the applied AC may be arbitrary.
  • Example 2 The synthesis was carried out in the same manner as in Example 1, except that diphenylacetylene used in Example 1 was replaced with bis (2-methylphenyl) acetylene.
  • Example 2 The synthesis was carried out in the same manner as in Example 1, except that diphenylacetylene used in Example 1 was replaced with bis (3-trimethylsilylphenyl) acetylene.
  • Example 6 Except that 2,3-diphenyl-1,4-diodo1,4-di (metabibifenole) used in Example 6 was replaced by butadiene with 3,3,1-jib-mouth 2,2, -bibenzothiophene The compound was synthesized by a method according to Example 6.
  • a transparent support substrate was prepared by depositing ITO to a thickness of 10 Onm on a 25 mmX 75 mmX 1.1 mm glass substrate by a vapor deposition method (manufactured by Tokyo Sanyo Vacuum Co., Ltd.). This transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition device (manufactured by Vacuum Equipment Co., Ltd.), and quartz containing N, N, dinaphthyl-N, N, and diphenylbenzidine (hereinafter abbreviated as NPD).
  • NPD quartz containing N, N, dinaphthyl-N, N, and diphenylbenzidine
  • Pressure of the vacuum vessel was reduced to 1 X 10- 3 P a, and heating the crucible NPD containing, by depositing NPD to a film thickness of 50 nm to form a hole transport layer, and then, in Example 1
  • the crucible containing the synthesized compound is heated and evaporated to a thickness of 15 nm to form a light-emitting layer.
  • the crucible containing PYPY is heated to a thickness of 35 nm.
  • PYPY was deposited to form an electron transport layer.
  • the deposition rate was 0.1-0.2 nmZ seconds. .
  • An organic EL device was obtained by vapor deposition at a vapor deposition rate of about 0.2 nm / sec and forming a magnesium and silver alloy electrode of 150 nm on the organic layer.
  • the transparent supporting substrate used in Example 9 was fixed to the substrate holder of the vapor deposition apparatus, and a quartz crucible containing ⁇ , ⁇ '-dinaphthyl ⁇ , ⁇ , and diphenylbenzidine (hereinafter abbreviated as NPD) was used.
  • Pressure of the vacuum vessel was reduced to 1 X 10- 3 P a, and heating the crucible NPD containing, by depositing NPD to a film thickness of 50 nm to form a hole transport layer, and then, in Example 8
  • the crucible containing the synthesized compound is heated and evaporated to a thickness of 15 nm to form a light-emitting layer, and then the crucible containing PYPY is heated to a thickness of 35 nm to form a PYPY Was deposited to form an electron transport layer.
  • the deposition rate is 0; ⁇ 0.2 nm / sec.
  • An organic EL device was obtained by vapor deposition at a vapor deposition rate of 0.2 nm / sec and forming a magnesium and silver alloy electrode of 150 nm on the organic layer.
  • the emission luminance was reduced to about 1 to 5 as compared with Example 8.
  • a device was prepared in the same manner as in Example 8, except that the compound represented by the chemical formula (3) synthesized in Example 1 was replaced with 9,9'-silaspiropen bifluorene.
  • the emission luminance was reduced to about 1/20 as compared with Example 8.
  • a device was prepared in the same manner as in Example 8 except that the compound represented by the chemical formula (3) synthesized in Example 1 was replaced with 1-aryl-1,2,3,4,5-pentaphenylsilacyclopentadiene. Created.
  • Example 1 1 The emission luminance was reduced to about 1 Z 17 as compared with Example 8.
  • Example 1 1
  • Example 9 The transparent supporting substrate used in Example 9 was fixed to a substrate holder of a vapor deposition apparatus, and a quartz crucible containing N, N'-dinaphthyl-N, N, diphenylbenzidine (hereinafter abbreviated as NPD) was synthesized in Example 8.
  • NPD N, N'-dinaphthyl-N, N, diphenylbenzidine
  • PYPY 3,4-diphenylsilacyclopentadiene
  • Example 8 Pressure of the vacuum vessel was reduced to 1 X 10- 3 P a, and heating the crucible NPD containing, by depositing NPD to a film thickness of 50 nm to form a hole transport layer, and then, in Example 8 A crucible containing the synthesized compound and a quartz crucible containing 9,9-spirobisilafluorene were simultaneously heated and vapor-deposited to a thickness of 15 nm to form a light-emitting layer, followed by PYP Y The crucible was heated and PYPY was deposited to a thickness of 35 nm to form an electron transport layer. The ratio of the compound in the light emitting layer was controlled by the deposition rate at the time of forming the light emitting layer.
  • the compound represented by the chemical formula (12) synthesized in Example 8 contains 2% by weight.
  • the anode of I TO electrodes, a cathode and an alloy electrode of magnesium and silver upon application of a DC voltage of about 5 mA / cm 2 current flows, the luminance of about 100 cd Bruno 111 2, wavelength 4 70 nm of blue formula ( Light emission derived from the compound represented by 12) was obtained.
  • Industrial applicability The silole derivative of the present invention has a high luminous efficiency and is therefore suitable as a luminescent material for an organic EL device. It is also useful as optoelectronic functional materials such as electrophotography, nonlinear optical materials, and conductive materials.
  • the organic EL device of the present invention uses a light emitting material having high luminous efficiency, a display with low power consumption and a long life can be produced by using this.

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Abstract

L'invention concerne un dérivé silole spécifique, par exemple, un dérivé correspondant à la formule générale (1), que l'on incorpore dans un élément organique électroluminescent, de sorte que cet élément possède une grande efficacité et une longue durée de vie. Dans la formule (1), R1 et R2 représentent chacun indépendamment alkyle, silyle, aryle, hétérocycle ou alcényle, éventuellement substitués, et ils peuvent être liés l'un à l'autre au niveaux des extrémités; Ar1 et Ar2 représentent chacun indépendamment aryle ou hétérocycle, éventuellement substitués; et R3 à R10 représentent chacun indépendamment alkyle, aryle ou hétérocycle, éventuellement substitués, et ils peuvent être liés l'un à l'autre au niveau des extrémités.
PCT/JP1999/003671 1998-07-09 1999-07-07 Derives silole et element organique electroluminescent les contenant Ceased WO2000002886A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
DE69929067T DE69929067D1 (de) 1998-07-09 1999-07-07 Silol-derivate und organisches elektolumineszenzelement, das diese enthält
EP99929736A EP1113017B1 (fr) 1998-07-09 1999-07-07 Derives silole et element organique electroluminescent les contenant
US09/743,426 US6376694B1 (en) 1998-07-09 1999-07-07 Silole derivatives and organic electroluminescent element containing the same

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Application Number Priority Date Filing Date Title
JP21038898 1998-07-09
JP10/210388 1998-07-09

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EP (1) EP1113017B1 (fr)
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WO (1) WO2000002886A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007119392A (ja) * 2005-10-27 2007-05-17 Univ Nagoya 多環縮環化合物およびそれらの製造法ならびに多環縮環化合物を用いる有機電界発光素子
WO2010047335A1 (fr) * 2008-10-21 2010-04-29 国立大学法人京都大学 Composé de benzène

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DE69929067D1 (de) 2006-01-26
KR20010071788A (ko) 2001-07-31
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